| 32. Round | 19/02/2000 | Stockport County | - | Blackburn Rovers | 0:1 | ||||
| 33. Round | 26/02/2000 | Port Vale FC | - | Stockport County | 1:1 |  |
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| 34. Round | 03/03/2000 | Stockport County | - | Barnsley FC | 1:3 | ||||
| 35. Round | 07/03/2000 | Fulham FC | - | Stockport County | 4:1 | ||||
| 40. Round | 14/03/2000 | Stockport County | - | Bolton Wanderers | 0:0 | ||||
| 37. Round | 18/03/2000 | Sheffield United | - | Stockport County | 1:0 | ||||
| 38. Round | 21/03/2000 | Stockport County | - | Manchester City | 2:2 | ||||
| 39. Round | 25/03/2000 | Wolverhampton Wanderers | - | Stockport County | 2:2 | ||||
| 41. Round | 08/04/2000 | Crystal Palace | - | Stockport County | 3:3 | ||||
| 42. Round | 15/04/2000 | Stockport County | - | Ipswich Town | 0:1 | ||||
| 43. Round | 22/04/2000 | Crewe Alexandra | - | Stockport County | 3:2 | ||||
| 44. Round | 24/04/2000 | Stockport County | - | Swindon Town | 3:0 | ||||
| 45. Round | 29/04/2000 | Huddersfield Town | - | Stockport County | 0:2 | ||||
| 46. Round | 07/05/2000 | Stockport County | - | Nottingham Forest | 2:3 |
England